The New Sensational Sister
by TheScottishKid
Summary: When Ash hears that the Sensational Sisters need his help, he is happy to lend a hand but he finds out they may be asking more than he bargained for. When an old rival appears he may regret offering to help... or will he. Ash x Gary This is my first ever FanFic so please review and I've left the ending open for the possibility of a full story if that's what the people want.
1. In At The Deep End

Ash stood at the bottom of the winding path leading up to the Cerulean City Gym, he smiled as he looked up to the huge Dewgong on the roof, he thought back about the call he had received from Daisy a few days earlier, Misty and the other sisters had been requested in Alola for some kind of emergency and Daisy was left looking after the Gym alone. She had asked Ash to come to the Gym immediately and more worrying, he was told to leave his Pokémon at home. He thought back to Pikachu being held by Mr Mime, it had been hard to leave it behind but if Misty's sister needed his help, he would do all he could. He sighed before pushing the door open and entering the gym. He walked through the halls and into the giant arena, "Hello?" he called out in front of the empty pool.

"In here, Ash!" was the response echoing from a room just off the arena. Ash walked towards the voice catching his reflection in the water, he noted just how different he looked from the first time he was here. He had grown noticeable taller and his hair was significantly longer, growing straight down with the help of his new love for product. He was still fresh faced, with small bags growing under his eyes. The evidence of his last few days sleeping rough on his way to the gym. He walked into the room and noticed Daisy hastily packing a suitcase.

Daisy looked up, her face turning from stressed to happy. She was quick to make her way across the room throwing her arms round Ash in a hug. "Oh, thank goodness you came." She exclaimed.

"Of course Daisy, I left as soon as possible just like you asked. So, what was this about, it sounded serious" He asked stepping away from the hug awkwardly.

"Please come in, I'll explain everything." She moved her hand gesturing to him to sit in a nearby salon chair.

Ash entered and followed Daisy into the Gym, "Hey, is Misty around?" He asked, "It's been a while since I saw her too."

"No, she's travelled to Alola to help out the locals there." She closed her suitcase and sat on top of it.

"Oh…that's right." He said, "So, how can I help you out, Daisy?" He asked eager to hear why he was there.

"Well, all my sisters have gone to Alola and I am also needed but I cannot leave the gym alone. That's when I thought of you. I need you to…" She paused slightly before continuing "run the gym while I'm gone?"

"You want me to run the Gym!?" He asked his mouth falling open, "Wow, I've never ran a Gym before Are you sure?"

"I know you've never ran a gym but you've been a trainer for a long time and I think you'll be great." She assured him

If you think I can do it then sure, I suppose I can act as a temporary Gym Leader" He said smiling.

"That's great!" She shouted in relief, jumping to her feet. "Now, I have been in contact with an old buddy of yours that will help you while we are gone."

"That's for trusting in me." He said, then he looked confused, "old buddy? Which old buddy?" He asked

She smiled to him, taking a Poke ball from the top of the cabinet, throwing it in the air. A familiar looking Squirtle wearing sunglasses popped out. "Squirtle, squirt!"

"Squirtle!" Ash cheered, hugging the little Pokémon, "How are you, old friend?" He asked with a smile.

"Squirtle, Squirtle squirt." It chimed happily.

"You can look forward to battling together a little later." Daisy said, returning Squirtle to its ball.

Daisy smiled and tilted her head. "Now, you can select five more Pokémon from our water type archives. I left some and there is also Misty's..." she sighed "Psyduck."

"Really? I'm surprised she didn't take him with her." He said, "Well, I think I can manage the rest on my own, anything else that I might need" He asked

"Emm, yeaaaaaaaaaaaaah. There is one thing." She moaned awkwardly.

"What is it?" Ash asked, "I'm sure I can handle it."

"Emm, follow me." She lead him to one of the rooms, and opened the door to reveal a walk-in wardrobe with lots of outfits, dresses, underwear, swimsuits and shoes.

Ash looked around "wow you sure have a lot of clothes. They are really nice." He admitted, letting his hand run through the fabric of one of the dresses.

"Thanks, Ash. I'm glad you think so... you'll... you'll be wearing one of them." She blushed, looking down to her feet shuffling them.

Ash's eyes widened looking at Daisy confused, "I'm sorry?" He asked, thinking he might have heard her wrong.

"Yeah, you have to pretend to be one of the sisters in order to run the gym. It's in the contract that only we may run it. I'm sorry I didn't tell you earlier." She sighed, looking apologetic.

"Oh…So you want me to be a Sensational Sister?" He asked, a small smile growing on his face, turning slightly red. He thought back about the days dressing up in his mother's clothes, parading around in front of the mirror, how awesome he felt, how comfortable he felt. "Okay!" He shouted suddenly, giving Daisy a slight scare.

"Yes, the most fabulous, sensational sister there is!" She smiled and pulled out a tape measure. "We just need to get your sizes!"

Ash blushed a little deeper, then, surprising Daisy, he smiled, "Ok…That sounds fun" He said

"R... really? That's great!" She threw her arms in the air and rushed Ash, she pulled the tape measure across his body in numerous places, she wrapped it around his chest, then waist. Nodding every now and then.

Ash stood still as Daisy measured him, "Yeah…I guess you're surprised I'm going along with this." He said blushing

She got on her knees in front of him and looked up. "Yeah, actually. I thought I was going to have to lock you in here and tie you up get you into the clothes by force but this is easier." She moved the tape to the floor and guided it up his leg, just grazing his crotch.

Ash blushed, "Well…the truth is…I like it. I like dressing like a girl. It's a secret of mine that no one else knows" He admitted

She was halfway round his ankle measurements when she stopped, dropping the tape. "Aaaaaah!" She screamed in her typical girly fashion. She grabbed his hand and dragged him to the clothes. "While we are gone, these are all yours. Your measurements are the same as Violet except the breast region." She motioned to Ash's flat chest letting out a short laugh. "We also have this." She opened a small locker, revealing an assortment of hair care products. Ash's eyes light up, his gaze floating over all the products he could ever want or need. "You can use any of these to make your hair look perfect. I'm so glad to decided to grow it long."

Ash blushed "Wow, I can't believe you're letting me have all this. There is one thing though you need to promise me you won't tell anyone?" He asked sweetly.

"Of course not. It's between you and me" She smiled "and Violet and Lily" She added under her breath.

He blushed at that, "Well…I don't suppose you'll have time for a little makeover?" He asked hopefully.

"I was hoping you'd asked. No time to waste, sit in the chair." She pointed to the makeup chair in front of the lighting mirror. Ash smiled as he sat back on the chair.

Daisy pulled open the makeup chest and started matching makeup to Ash's skin tone. "This is going to be so much fun."

"Oh yes…I can't wait to be Ashley again" He said smiling before his face fell, realising what he had just said.

"Ashley. I like that." She smiled. "Don't worry. Your secret is safe with me." She assured him, catching a look at his worried face. She quickly got to work, applying makeup all over his face, giving some fake eyelashes to top off the look. She was quick to pull his hand forward giving him a manicure before adding brown nail polish to match his eyes, she repeated the action with the other hand and stood back to admire her handy work.

"Perfect if I do say so myself." she laughed at her own words spinning the chair round to let Ash see himself in the mirror.

"Wow, I can't believe it's me. I look just like a girl!" He said happily looking at himself, seeming to finally feel like his true self.

"Can I change out of my clothes?" He asked hopefully

"Of course, of course. You have a large range to choose from. Pick your favourite!"

Ash smiled as Daisy left to give him some privacy. He looked around just to make sure he was alone before taking everything off. Since most dresses doubled as swimsuits, he was free to wear those alone. He looked around thinking of how the Sensational Sisters looked in their dresses, he decided on one that was light blue. Not wasting any time, he quickly slips the dress on. He opened a small drawer blushing a little at the selection of panties that he found. He picked one that matched the dress perfectly, slipping them on and blushing even deeper.

Ash giggled and did a little twirl as Daisy entered the room again "Oh Daisy, I feel…well…Sensational" He said in a girlish tone

"I love it Ash-ley" She added, "You're a real Sensational Sister now." She picked up a suitcase from the floor and smiled. "Well, I've got a Lapras to catch."

Ash smiled with gratitude "Well, I guess this so goodbye" He hugs Daisy, "Thank you so much."

"You are going to fool everyone, you look perfect!" She hugged Ash and put on her stylish coat. "Good luck and call me if you have any problems." With that she headed to the front door.

Ash now had the gym to himself. after choosing the Pokémon and explaining to them everything that was going on and a special explanation to Squirtle, Ash was free to do what he…or rather, she pleased. He had set his six poke balls in their spot by his battle area and was humming a song with his feet dangling in the pool. A sound of the front door opening gave Ash a shock. He quickly stood up, heading to the entrance to the arena, waiting on his first possible opponent. A knock came at the arena door and Ash took a deep breath and opened the door.


	2. A Familiar Face

"Welcome to the Cerulean Gym. I'm A- He began in his girl voice, then froze as he saw who it was.

"Well, it's about time!" He moaned, not noticing. "It is me! The legendary Gary Oak. I am here to challenge you for one of your badges!" He looked at the character in front of him. "Who are you? Where are the four Fabulous Sisters?!"

Ash tried to compose himself, He smiled as he spoke, "Well, Gary Oak" He began in his girl voice, "Sadly, the sisters have put me in charge. The name is Ashley and I'm an Honorary…Sensational Sister" He said with a twirl, blowing a kiss his way and winking.

Gary felt a weird feeling. He seems to think the woman look slightly familiar and the kiss took him slightly off guard. "Umm, yeah, okay... do I… do I know you?"

"Hmm…no, I don't think so. I'd remember somebody as cute as you" He said with a giggle, his face was pink as he realized he was actually flirting with another boy, especially Gary of all people.

"Emm, yeah sure. Stop trying to distract me! I am going to crush you with my mighty Pokémon!" He stepped into the doorway. "Let's get this over with!"

Ash looked at him suspiciously, raising an eyebrow. "Say, don't you already have a badge from this gym?"

"Yeah, I did. I had my Kanto badges stolen a while ago. So, I need to go around and get them all back." He scoffed sounded disgusted.

Ash sighed, "Oh very well" He said, "Of course that doesn't mean I'll let you win to get it back" He added with a flutter of his eyelashes.

They approached their own battle areas and readied themselves for battle. Ash picked his first Poke Ball and nodded. "Now, there is no referee so we will have to settle this on our own. Three against three." He hummed across the battle field.

Gary growled as he expanded his first Poke ball. "Sounds fine to me. Let's go!" He grinned waiting on Ash to throw first.

Ash was quick to throw his ball, Squirtle landing in the water with a splash letting out a loud happy call.

Gary smirked, throwing his own ball in the air. "Land on one of the platforms!" He called out as Electivire came into sight and did what it was told, landing with a loud thud.

The first battle proved easy enough for Gary, the type advantage evident. Ash let out a loud sigh as Squirtle landed by his side, fainted.

Ash's next choice was another friendly face, Misty's Staryu. He thanked her in his head for leaving it for him. Using a combination of normal and physic moves, Electivire was knocked out after a tough battle. Ash complimented Staryu giving a twirl in celebration, feeling especially girly.

It was Gary turn to look annoyed as he decided upon his next Pokémon. Doduo sprang into action. The two Pokémon fought hard and after a hard-hitting thrash Staryu fainted much to Ash's dismay. Gary was ready to celebrate just as his confused Doduo headed into the bottom of the pool, knocking itself out. "Son of a…" Gary cut off, returning his Pokémon with a curse.

Ash grabbed his last choice Poke Ball. "It all comes down to this!" He called across the battlefield.

"Get ready to lose!" He called back, reaching for his own last choice.

"Let's go Gyara-" Ash was about to throw the ball as a red mist appeared from behind him, a small yellow creature landing on a platform in the pool.

"Psyduck!" Ash called out in shock, he tried not to growl as he heard Gary laugh from across the battlefield.

"This is going to be easier than I thought." He grinned as he quickly changed his mind, choosing another poke ball he threw it, revealing Umbreon.

Indeed, it ended up being an easy and quick fight. The Psyduck that can't swim was swiftly defeated by the dark type Pokémon. Gary smiled and raised a hand in the air victorious. Ash could only sigh, returning Psyduck shaking his head in disappointment.

Gary couldn't help but think how he was thrown off by the girl, clearly not his best performance. He was snapped out of his thought as Ash walked up to him, "Congratulations Gary, you win." Ash droned, trying to sound upbeat and feminine.

He smirked and returned his Pokémon. "Of course, I won. I'm Gary, motherfuckin', Oak! I'll just take my badge and get out of here!" He said, clearly uncomfortable, trying to sound confident.

Ash frowned a little at that, but smiled, "You sure you don't want to stay for a little while?" He offered, "We can talk about whatever you like…we can even have a little fun" Ash was unsure where this came from, he realised he was getting more into his female persona, he also realised that he was feeling attracted to Gary.

Gary backed away a little. Unsure of the girl's actions. "Emm, no thanks, I need to emm, get going to the emm, Pokémon centre..."

"Well…I guess that's fair." He said, then held the badge "Well here you go." He holds it to Gary, but pulls away as he reaches for it "But…I need one last thing from you, Gary Oak" He said as he stepped closer

Gary reached out and then sighed at it was pulled away. "Okay, what would that be, Miss?"

Ash smiled as he stepped closer and said "This" He suddenly pulls Garry into a kiss, he lets out a light and girlish moan, lifting a leg in the air.

"Wha-" He tried to speak before feeling lips on his. He smiled and put his arms around the girl, pulling her into the kiss, closer to his body "Mmm…" Ash moaned as he kissed deeper, his mouth opening slightly. Gary took this chance to let his tongue enter Ash's mouth, letting it wander over as much as it could. Their tongues met and joined, it was heaven, soon the need for air was great and Ash had to pull away, he ended the kiss with a soft "Mwah!" and smiled. Ash hands Gary the badge, "Good luck on your journey" he said sweetly and turned to leave.

Gary stood with his newly won badge in his hand and a newly strange feeling in his pants. "I uhh..."

"Something wrong?" Ash asked sweetly turning back to face him.

Gary narrowed his eyes. *Okay, if this is the way you want to do it.* He thought to himself. He quickly closed the gap between them, he put his arms around Ash and pulled their bodies together, forcing him into another deep kiss.

Ash gasped, not expecting it, but it was a good surprise, he happily kissed back, letting out short moans.

Gary put his hand on the back of Ash's head, forcing it upwards, making it easy for his tongue to make its way into Ash's mouth once more.

Ash felt a small jolt of pain from his head, but didn't complain as he felt his own length grow hard under the light blue panties. He grew slightly nervous, worried that Gary might feel it.

Gary pulled away and smirked, feeling like he had won his second battle of the day.

Ash decided that his fun was over and decided to try to get rid of Gary before his crotch became the centre of attention. "Enjoy your badge and I wish you luck in your other gym battles." He said with a smile. "I'll sure I will see you around." He added with a wink.

"Thank you," Gary replied with a smirk. "I might come and visit once I have all my badges." With that Gary picked up his things from the side of the battlefield and slowly walked to the exit.

"I'll look forward to it. Goodbye" Ash called out before blowing him a kiss and waving goodbye

Ash returned to the bedroom he was left by Daisy. "Oh Gary…" He let out, "What a kisser" He closed his eyes, reliving the scene that had just played out. Slowly he reached down under his dress, rubbing himself through the silk panties. He was quick to pull his length out the side, pacing his hand up and down, letting out soft moans.

Gary reached the end of the street, thinking about the mystery girl the whole way. "Fuck," he cursed under his breath, unable to shake the vision of her out his mind. He turned around quickly pacing back to the gym.

"Oh Gary" Ash moaned out to the empty room. His movement speeding up, finding it difficult to control his bucking hips.

He couldn't get the thought of her out his head. He reached the door, ready to knock but noticed it was still open from when he left. He slipped into the arena and closed it quietly behind him. He heard a sound from a nearby hallway and decided to head towards it.

Ash let out loud moans, his head shook as he was close to his climax, his hair falling over his face as he now imagined Gary pushing inside him, thrusting hard and deep into him.

Gary got close to the noise that Ash was emitting. "Hello?" He called out in the emptiness.

Ash was too occupied by his climax to hear anything, he climaxed into the air just as Gary poked his head into the door and looked at him.

"Hey, Sorry for barging i-" Gary stopped in the doorway, frozen with shock.


	3. Keeping Him Quiet

Ash froze suddenly, coming back down to earth with a thud. He couldn't move, he just stared at Gary as he stared back.

Gary looked down, still not recognising Ash, He quickly turned and headed back down the empty corridor.

Ash gathered the strength to get up, cleaning himself on the sheets quickly before following Gary. "Um, Gary?" He called out, using his normal voice.

Gary stopped walking as he heard his name from the familiar voice. He turns to the Ash and studies his face before letting his jaw drop open. "K... Ketchum!?" He stuttered.

Ash blushed deep red as he sighed, "Yeah…it's me…"

"W...what the fuck are you doing? Dressed like that! Y…you, oh my god, you kissed me!" Gary recoiled back, spitting dramatically.

Ash blushed, "I… Daisy dressed me up." He said, "Saying it was part of me watching the Gym." He said "And well…I let her do it." He looked rather insulted at Gary's theatrics but quickly understood his actions. "And you know, you kissed back" He added.

"Of course, I kissed you back! I thought you were a girl!" Gary retorted.

Ash was silent, He didn't know what else to say. He suddenly felt very ashamed and wrong for what he had done, how he was dressed.

"Was this some sick prank to get back at me for being better than you at everything!" Gary shouted down to him.

"No, of course not!" Ash said, "I…It's just…a fantasy of mine." He admitted

Gary let out an obnoxious laugh, trying to make himself feel better about the situation. "Of course it is. Everyone fantasises about being with the legendary Gary Oak."

Ash glared, but let his comment slide, "So…I suppose you'll tell everyone now." He said feeling tears prick at his eyes.

"I might, I might... unless you've got something to offer me. I seem to be short on Poke Dollars lately." He grinned, feeling good at his opportunity to take advantage of Ash.

Ash sighed, rolling his eyes. "A bribe, really?" He asked, "Well, unfortunately I'm short on cash myself" He said, turning his nose up at Gary.

"Well, that's fine. Guess I'll have to drop in to your mom when I get to Pallet Town. Tell her what her son is up to." Gary smirked evilly,

"What?! No, no, please, you can't tell my mom. Anything but this. I'm not anywhere near ready to tell her about any of this." He cried out, tears now falling from eyes.

"Too bad Ketchum. I bet all your little lady friends would love to hear about this too and you can't do anything to stop me." He snarled, thinking about the females that Ash had travelled with, he wondered why he had never got with any of them and this explains it.

Ash stood front of him, 'What else can I offer you? There has to be something…Anything." He sobbed, more tears falling.

Gary's eyes drifted down to Ash's lips before snapping back up to his eyes, starting to feel a pang in his heart as he watched Ash cry. "N… Nope. I'll just be on my way." Gary tried to step around him but couldn't bring himself to do it.

"Come on, I'll do anything" Ash begged, dropping to his knees.

Gary looked down, feeling sympathy for the boy in front of him. "Hmm, look Ketchum, just... hmph." Gary pouted as he saw watched him. He couldn't help but thing how innocent Ash when he was on his knees in front of him , "Please, anything."

Gary felt his hand move on its own, running a hand through Ash's hair, "Y… you shouldn't cry. It might smudge your makeup." He said in an awkward laugh.

Ash blushed, he felt a smile crawl over his face as he looked up, his tear drying up "Is this better?" He asked wiping his eyes, his girly voice returning.

"It is actually. Makes me kind of forget who you are underneath it all." Gary smiles, more genuine than before, running his hand across Ash's cheek.

"Really?" He asked sweetly

"Yeah, actually. You really look good as a girl." He smiles running the hand down across his face. "but I'm not gay!" Gary exclaims pulling his hand back.

Ash giggled as Gary spoke, "No one needs to know," he smiled, batting his eye lashes. "And I'm not a boy…I'm a girl, Ashley" He said sweetly, perfecting his high pitched tone.

"Damn you, Ketchum. Now get up here and kiss me!" He demanded pulling on Ash's dress.

Ash nodded and done as he was told, raising to his feet and planting his lips on Gary's, letting out a relived sigh.

*It's a girl, it's a girl, it's a girl* Gary repeated in his head. Leaning into the kiss, letting out a desperate moan.

Ash moaned, his fears were melting away into passion…and lust, he wanted more, his hands moved to Gary's pants

Gary hesitated slightly as he felt Ash's hand move. "W... what are you doing?"

Ash blushed, "Y... You say me exposed, so it's only fair I see you like that too." He said blushing harder.

Gary almost choked hearing this from Ash. He tried to speak but just stuttered. All his arrogance just melting away. Ash took this as a sign and started to unzip his pants. Gary felt his underpants grow increasingly tighter as he grew at Ash's bold moves. Ash returned to his knees and began pulling the pants down, seeing the imprint Gary left on his boxers. He couldn't help but feel a little envious as he noticed how much bigger Gary was than him.

"Wow" he whispered as he traced the outline with his fingers, earning him a sharp intake of breath from Gary. Ash gulped as he pulled down Gary's boxers, realising there was no going back now. He gasped as Gary's length hit the side of his face as it sprung free. Gary quickly stepped out of his bottom half, letting Ash throw them to the side. Ash took it in his hands, his eyes sparkling at what he saw. He slowly started moving his hands up and down, like he had down to himself not long ago. He smirked as he heard quiet moans from Gary's mouth. He quickened his pace, noticing small clear droplets forming on the tip. Ash licked his pink lips and bravely took the tip into his mouth, licking the drops away.

"Oh my Go-…" Gary trailed off as Ash got to work, He smiled as he looked down at the makeup covered face.

Ash moaned girlishly as he happily moved his head further down taking as much in his mouth as he could, feeling a jolt as his panties started to grow tight again.

"Oh, this is amaze-" Again he trailed off as he gripped the back of Ash's head, forcing his mouth further down. He moaned loudly as Ash took him fully in his mouth. Ash gagged but loved every second of it as he sucked, licked and nibbled gently.

It had been a good while since Gary had felt realise and knew he was close. "Oh, Ash... ley. I'm not going to last!" He blurted out.

Ash pulled back, getting some much needed air. "Do it, cum in my mouth." He said, taken aback by his own words.

Gary pushed Ash's head back down, forcing himself right down Ash's throat.

Ash gagged and felt Gary realise into his mouth. They both moaned loudly. Ash's eyes rolled back, adoring the taste and the feeling. His first sexual experience had been with his longest rival, and it was amazing.

Gary fell back, his legs giving way, landing on on the floor. "D... damn." His first sexual experience had been with his longest rival, and it was amazing.

Ash happily swallowed every drop, trying to speak but unable to find words.

Gary stared at Ash and realised that he no longer saw Ash, the loser from Pallet Town. He saw Ashley, the amazingly hot Sensational Sister. "W…Wow. You where... so... good." he said in staggers trying to catch his breath. Ash nodded, finally finding words. "Thank you, I'm glad you liked it." He joined Gary, sitting on the floor next to him, moving closer. Gary happily put his arm around him. Pulling him into a hug. They both sat on the floor in silence, contemplating what just happened and what would happen next.


	4. The Morning After

The sun rose early the next morning, light poking through the curtains of the Cerulean City Gym's bedroom. It caught Ash's face, no longer filled with makeup but cleaned by a late night shower, he stretched and yawned as he slowly woke up, his mind filling with memories of the previous day's events he smiled looking across the king-sized bed, seeing Gary still sleeping silently. Ash let out a small giggle as he thought of their day together. How it began with a battle of Pokemon, turning into a battle of a different kind, eventually leading to the hallway and after a long silence on the hall's floor they had ventured back into the bedroom and...". His train of thought was cut off as he heard a short cough as Gary opened his eyes and sat up.

Ash hid his face as Gary looked his way. "Emm, Morning." Gary stuttered awkwardly. Ash kept his face turned away.

"Y...Yeah, Hi" He said, trying to change his voice.

"What are you doing?" Gary asked putting a hand on Ash's shoulder.

"I don't want you to see me without my makeup. I don't want you to not like me anymore" Ash turned away fully. Lying back down with his back to Gary.

"Mhhm. Okay, well, I." Gary went between words awkwardly, not knowing what to say.

Ash took Gary's silence for agreement with his statement and sighed, he quickly entered the walk-in closet room and began his transformation. He looked through a large number of dresses and accessories and chose a small, purple dress and matching lingerie and footwear. He turned to the mirror and opened the large makeup bag set out for him, as he was focusing on his face, applying the makeup his mind turned back to Gary, first off wondering what he was doing while he was away and then to a possible future.

"Would he accept me for the normal me or only be able to stand me if I'm dolled up?" Ash thought to himself, letting out another sigh. "Maybe I'll just have to make him fall for Ashley then he'll have no choice but to end up with me". Meanwhile, Gary had Gary lay back down on his side of the bed, staring up at the ceiling,

"What have I gotten myself into?" He said quietly, exhaling sharply. "This is weird on so many levels, this is Ketchum, the same snot nose kid who could never come close to my greatness." His eyes blinked a few times and then closed, "Although something has obviously changed, he's so..." His train of thought was interrupted by Ash emerging from the closet, complete the look of his female alter-ego by straightening his long hair and adding a purple bow to his head.

"Is this better?" Ash asked

Gary looked Ash up and down, taking in the full view, he couldn't believe that was the same person he had woken up too. He had tried all night to make up his mind, should he be with him, her or would he have to take both. He snapped out of his trance and stood up, striding across the room to where Ash was standing. Gary grabbed him, pressing their lips together. His mind had been made up as soon as he laid eyes on the new Ashley that had come out of the closet, Gary laughed through the kiss as he realised his accidental pun. Ash parted the kiss and looked up and gave a small smile.

"What's so funny?" He asked in his changed voice.

"Oh.. nothing," Gary said innocently, looking down at Ash and running a hand through his hair. "But I have to say, you look amazing and I love that voice you put on."

Ash's heart fluttered slightly as he heard the L word. "Ah... Well, that's good. I like your new change of attitude as well." He moved forward placing his hand on Gary's chest.

Both of their hearts started beating faster, they locked eyes and leant forward, locking into a deep kiss they could feel all the awkwardness and anxiety fade away as Ash's subconsciously pushed Gary towards the bed until the back of his knees hit the mattress and he flopped into a seated position, looking up at Ash, at first he noticed only the feminine details and focused on the red lipstick but he slowly looked past it seeing Ash for what he truly was. Gary put his hands against the bed and began pushing himself up, trying to escape, as he did Ash moved forward and planted his lips against his own. Gary's objections were non-existent by this point as he craned his neck upwards kissing Ash deeply, parting his lips so the boys' tounges could find each other, fighting back and forth. Gary felt a tug at his abdomen as Ash was pulling up his day-old shirt, he raised his arms to allow it to come off and Ash couldn't help but break the kiss as his eyes drifted down Gary's body, taking in as detail as he could, noting how much more feminine his own body type was and just how attractive Gary had become.

"It's not like you to take control, Ketchum." Gary whistled, snapping Ash out of his daydream.

Ash smiled but gave no reply, how happy he was that Gary was still acting like his usual jerky self, like he was getting more and more comfortable with him. Before Ash could go back to daydreaming he was pushed to the side, flopping onto his back and quickly pounced on by the stronger and quicker boy. As quickly as he had thrown Ash away, Gary slipped out of his bottoms and began fiddling with the dress. Ash giggled as he watched him struggle, eventually helping him unzipping it from the back and pulling it carefully down his slender body. Now it was Gary's turn to lose focus, he found himself for the first time, accepting that he found Ash, a male, attractive. He was eager to run his hands across Ash's body but found his hands shaking and unable to move. Ash looked up to Gary's face then down at his hand, taking them in his own and placing them both on his chest, lifting up his own hand and stroking Gary's cheek.

"It's okay," Ash chirped. "Take it slow, I get that this is new to you."

Gary had dealt with new and exciting adventures in the past but this was something very different, but slowly he moved his hands up and down Ash's chest, making a note to manually breathe. He ran his fingers lower, earning a sharp exhale from Ash. Gary's smirk returned as this gave him confidence, slowly working his way further down.

"Too late to turn back now." He thought to himself, taking a deep breath and reaching under Ash's underwear. "Even if I wanted to."


End file.
